Asking Felicity Out
by theboyfriend-and-theprettygirl
Summary: A collection of small drabbles in which Oliver asks Felicity out on a date and how she reacts. Some will be long one-shots and others will be short. I will try to think of different situations for each time Oliver asks Felicity out and a different reaction from her each time. Please give it ago :) [Oliver/Felicity]
1. Drabble 1: Oliver's Internal Struggle

**Title: **Asking Felicity Out

**Summary**: A collection of small drabbles in which Oliver asks Felicity out on a date and how she reacts. Some will be long one-shots and others will be short. I will try to think of different situations for each time Oliver asks Felicity out and a different reaction from her each time. Please give it ago :)

**Disclaimer/ Note from the author: **

Not a story guys, just a collection of small drabbles in which Oliver asks Felicity out on a date.

Each drabble will be different and they will not continue on from each other.

FYI, I will not be making these into a regular story. These are just for fun and inspired by the Spoilers for episode 3x01.

If you want me to write a fic based on an actual Olicity date just leave me a comment in the review section and if I'm feeling generous I might write your request :)

**Date Published: **16 July 2014

© theboyfriend-and-theprettygirl, 2014

* * *

**Drabble One: **Oliver's Internal Struggle

"Felicity, what are you still doing here?" Oliver asked turning on the main lights to the liar, and making her jump a little out of her skin. "Do you know what time it is?"

"Oh geez. It is late." she said checking her wrist watch. "Wow, I guess time really does fly when you're having fun. _Not _that I was having fun..I was just-"

"Felicity..." Oliver said placing a hand on her shoulders. "You're rambling on again."

"Oh, right." she said blushing a little. "Well, I should get going. I'm exhausted."

Oliver smiled. He knew she rambled whenever she was nervous about something. He found it completely adorable.

"Have you been here all night?" Oliver asked frowning a little.

"Pretty much. I had some software to update...it took longer than I thought."

"You could've done it in the morning. I would've helped you."

"Ha, sure." she said laughing a little, before rolling her eyes. "Because working with _me_ has made you a qualified IT geek. I don't think so, Oliver. But thanks for the offer."

"Hey, how about you take the morning off tomorrow?" Oliver said helping her put on her coat.

"Why?" she asked frowning.

"Felicity, its 3am. Aren't you tired? Don't you want to sleep in a bit?"

"I'll be fine. I just need a couple of hours and I'll be good to go. I don't really need beauty sleep...I'm not one of those girls who make it their life's purpose to look like a _model _every day. Besides, I still have more software to update. Oh and I need to check our firewall because-"

"-Felicity." he said placing both hands on her shoulders quickly to make her stop mid-sentence. "You are sleeping in tomorrow and that's an order."

"But.."

"No, buts. Diggle and I will be fine for a couple of hours without you. You've been working so hard lately, you deserve a rest. Now go home. It's late and you look exhausted."

"What are you doing up so late, anyways?" she asked as she flung her handbag over her shoulder.

"I couldn't sleep." he said running his hands through his hair a little nervously. "I came to use the salmon ladder."

"Is everything okay?" she asked touching his forearm gently. "You're not still having nightmares about Slade, are you?"

"No. It's something else that's keep me awake." he said softly.

_It's my internal struggle of whether to ask you out on a date or not,_ Oliver thought sighing heavily.

It had been a recurring dream ever since they had tricked Slade with their little performance at the Queen Mansion. On the Island Diggle had given them a minute to talk things through in private and despite wanting to tell her that he had _meant _every word, Oliver had chickened out. He knew exactly how Felicity felt about him and he wanted nothing more than to reciprocate those feelings...he was just scared to put her in harm's way. He cared about her too much to allow his feelings for her to place a target on her back. He had to keep her safe, even if it meant that they couldn't be together. That was the dilemma he faced whenever he considered whether to tell her the truth about his feelings for her or not...

"Oh, well whatever it is, the only way that you are going to be able to deal with it is if you face _your demons, _Oliver."

_His demons? _Oliver shook his head. She couldn't be more off track if she tried.

"I remember having these recurring dreams like every time I slept and the only way I got rid of them was to deal with the issue at hand. I was avoiding telling someone this thing that was kind of big...so I kept it from them and the secret was eating me up alive. I dreamt about telling them the truth every time I slept and it was really starting to get to me until I finally fessed up." Felicity mumbled on, snapping him out of his thoughts. "I guess the moral to the story is, once you sort out the problem, you'll be able to sleep at night again...the problem will stop haunting you."

"You know what? I think you're absolutely right." Oliver said smiling. "What are you doing tonight?"

"Uh, what do you mean?" she asked a little puzzled as she pushed up her glasses.

"After work, I mean. Do you have any plans? Tonight?" Oliver said, feeling his heart race quickly. She must have been rubbing off on him because he was starting to mumble like her, instead of being his usual calm, cool and collected self.

"I don't know. I thought I might watch a movie. I haven't decided yet. Why?"

"Let's go to dinner."

"Okay." she said smiling. "Where should I make the reservation?"

"Leave that to me." he said smiling a little. _See Oliver, that wasn't so hard, was it?_

"Okay, so should I tell Dig...or are you going to tell him?" she asked, instantly crushing him.

"I was actually thinking it would just be the _two_ of us."

"Oh." Felicity said quietly, a small smile forming on her lips. "I'd like that."

_The end._


	2. Drabble 2: The Perfect Moment

_**Author's Note:** _

_T__his drabble is really fluffy. You have been warned in advance ;)_

_Hope you like it. Please review if you want me to keep writing more of them._

_Paris xx_

**Drabble Two:** The Perfect Moment.

"Is there anything else you need for the night, Oliver?" John Diggle asked, putting on his leather jacket.

"No. I think we should call it a night." Oliver said patting his friend on the back. "Thanks for all your help, you guys. I don't think I could have done any of this without you."

Felicity smiled at him quickly, before continuing to shut down the computers in the liar.

It was still early in the evening. Usually they would all work much later through the night, but ever since they had taken down Slade and his army, Starling City had found a new wave of peace. This meant that they no longer needed to be guarding the City throughout the night or taking down the latest dangerous villain posing a threat to their City. Things were quiet and a little boring at the Liar for _Team Arrow_, as Felicity liked to call them. The City was safe. The residents of Starling City did not need him. The Arrow could finally have some quality of life.

"So..._hot_ date tonight, aye Dig?" Felicity asked, nudging him a little. "I want to hear all the _details_ tomorrow."

"Goodnight, Felicity." John said, rolling his eyes playfully at his friend and heading towards the stairs. "Night, Oliver."

"Night Dig." Oliver said, before turning his attention towards Felicity "So..."

"Is it cold outside?" Felicity said when an awkward pause fell over them.

"I think it's snowing."

"Oh, of course it is. It's Winter. _Duh._" she said hitting her forehead with the back of her hand.

Oliver laughed. He loved whenever she was sarcastic and reprimanded herself. He found it to be super adorable.

"So...any plans tonight?" he asked, helping her put on her coat.

"Not really. I was going to order Chinese and catch up on some tv shows. I'm really into _Dexter_ at the moment. So I've got like two seasons of that to go, but I heard that they show went downhill by then...so..."

Oliver laughed. "I never was a fan of the show anyways, but I wouldn't peg you as someone that enjoyed watching a serial killer chop up people."

"Not a fan of the show!" she scoffed loudly. "And FYI, he only chops up other_ serial_ _killers_...well, most of the time anyways." she said rambling. "Not everyone can be amazing and kick-ass like _The Arrow."_

"That is very true." he said hitting the lights behind them as they headed towards the stairs.

"What about you?" she asked, trying not to sound too interested.

Oliver couldn't help but smile. There was something about the way her eyes lit up whenever she asked him any personal questions. It made me feel so special to know that her crush on him hadn't gone away. One of these days, he was going to gather up the courage and ask her out. He was just waiting for the perfect moment. Timing was everything. After all, he had waited this long...He didn't want to stuff it up now.

_"Oliver?"_ she said waving a hand in front of his face to get his attention. "Earth to Oliver? Did you hear what I said?"

"No. Sorry." he said quickly.

It had only just hit him that he had been staring at her again. He had been doing that a lot lately. He was starting to wonder if she was starting to find it at all creepy.

_Note to self, you need to stop staring at her because you always get distracted and you zone out._ Oliver thought, mentally scolding himself.

"That's okay." she said sweetly. "I just asked what you were going to do tonight?"

"I was thinking about getting something to eat. Maybe Chinese?" he asked, smirking a little. "Do you want to join me?"

"Chinese, huh? Is that your way of asking me out?" she asked, raising a perfectly arched eyebrow at him.

"Maybe. Is it working?"

Felicity blushed and almost tripped on a step. He quickly reach down and catch her before she fell face first on to it.

"Sorry." she mumbled, her cheeks reddening. "Thanks, Oliver."

"Are you okay?" he asked, squeezing her arm gently.

"I'll be fine. You know me...I'm a major klutz." she said, avoiding his eyes. "So do you think it's going to be snowing for a couple of days?"

Oliver laughed a little. _She was nervous._ She would always talk about the weather whenever she wanted a way out. Clearly he had come on too strong with his flirting and he had startled her. He needed to ease her into it, not blindside her with his feelings.

_I don't know - _was all he managed to get out. They walked the rest of the way, through the club and out to the car park in a slight awkward silence.

"So, thanks for walking me to my car." she said when they had reached it. "I'll see you tomorrow?"

"Felicity..." he said, pushing back a strand of her hair that had gotten caught on her face when a gust of wind blew suddenly.

"Oliver, I'm freezing." she mumbled quietly.

"Here, take my coat." he said starting to take it off, before she stopped him quickly.

"Are you crazy? It's snowing. You're going to catch a cold."

Oliver looked up at the night sky. He hadn't even noticed that it was snowing until she had mentioned it. But now as they stood there in the middle of the deserted car park, the snow falling onto her beautiful blonde hair, making her look nothing sort of an angel; it finally _hit_ him.

This was the moment that he had been waiting for. This was the perfect time to do it.

It was now or never. He wasn't going to get a more perfect opportunity again.

Oliver closed the gap between them in one quick step and cupped her face tenderly. Before Felicity had a chance to respond, he pressed his lips against hers. The kiss was sweet and short. But she had kissed him back and that was all that really mattered to him once he pulled away.

"Oliver.." she said softly, her eyes searching his face.

"I've been wanting to do that for awhile." he said honestly, tucking another lose strand of hair behind her ear.

"So have I. What took you so long?" she asked pulling at his coat roughly and crushing her lips against his again.

Felicity moaned loudly as Oliver gently pushed into her car and deepened the kiss. The little sound that had escaped her lips, almost made Oliver want to rip her clothes off right there. _But Felicity was different._ She was worth the wait. Despite how much he wanted her and how much she was driving him crazy...he would gladly wait if it meant that they had a chance to make a _real go_ of things.

"Let's go and get some dinner." he said once they had pulled apart for air. "I'm thinking... Chinese?"

Felicity laughed loudly. "Does that mean you want to watch _Dexter _with me?" she asked hopefully.

"Don't push it." he said, rolling his eyes quickly.

"It's Chinese and _Dexter _or nothing at all buddy...take it or leave it."

Oliver sighed heavily. "I guess I could give the show another go...since I really don't have a choice."

"Then it's a date. Here, you can drive." she said throwing him her car keys quickly.

Oliver laughed and followed her around to the passenger's side of the car.

"Hey? What are you doing?" she asked, frowning a little. "I gave you the keys. You're driving."

"I know. I just wanted to get the door for you." he said, opening it for her quickly.

"So chivalrous." she said rolling her eyes playfully.

"Well, it is a _date,_ after all." he said smiling at her before closing the passenger's door and heading back around to the other side.

_The end._


	3. Drabble 3: Right under his nose

**Drabble Three:** Right under his nose

She had been there right in front of his face the whole time.

_Felicity Smoak_ -the socially awkward, babbling IT genius, who clearly had a school girl's crush on him- _had been right under his nose the whole damn time._

Oliver wanted to kick myself for being so stupid. _How was it that he had never realized his feelings for her before? _He thought, glancing over to the corner of the cafe where Felicity and Barry were laughing together loudly.

A feeling he could only describe as jealousy spread throughout his whole body, as he clenched his fists tightly into small balls. When Felicity had asked him out for coffee he had assumed that it would just be the two of them.

"Oliver, over here!" Felicity called out to him, waving her hand in the air to get his attention.

Forcing a fake smile, Oliver headed towards the back of the cafe and slid into their booth.

"What took you so long? Did you get lost?" She asked when he had sat down opposite them. "I messaged you like half an hour ago."

"Oh, I just had to run an errand first." he said lying.

"You remember, Barry, right?" She asked laughing a little nervously.

"How could I forget?" he asked dryly. "It's nice to see you again, Barry."

"Likewise." Barry said extending a hand for Oliver to shake.

Oliver really didn't want to shake his hand and it took all his self-control to not crush it deliberately. But seeing the way that Felicity's face lit up at the gesture, he decided to be the bigger man.

"So...what have you two been up to, Barry?" he asked, taking off his coat and placing it next to him. "I didn't know that you were back in Starling City."

"I came back today, actually."

"Visiting family or something?" Oliver asked, trying to push for more answers as discreetly as he could.

"Not really. I don't have any family here. But I guess you could say something else _caught_ my eye the last time I was here." he said smiling at Felicity.

Felicity smiled back quickly, her cheeks reddening a little, as she started to fumble with her necklace.

Oliver felt sick to his stomach as the realization that he was loosing her started to sink in. _He was too late. How could he have been so stupid?_

"So...that's why I came back." Barry continued, snapping him quickly out of his thoughts and bringing him back to the present moment. "I want to see where things go with that."

"Will you be in Starling City for long?" Felicity asked, turning her attention to Barry.

"That all depends on how things go with-"

"Should we order?" Oliver asked loudly, cutting Barry off mid-sentence, before Felicity gave him a disappointed look.

"Sure." Barry said picking up a menu. "What do you guys suggest? I would have no idea what's good here."

"I like the Chai Latte or the herbal teas." Felicity said leaning close to Barry and pointing at a few items on his menu. "Oliver likes the cappuccinos from here and Digg, our other friend...you met him awhile a go, remember?...anyways, he likes the short black espresso shots."

"I'm not much of a coffee drinker." Barry said grimacing a little."And I don't like herbal teas."

"That's okay, I didn't at fist too. It's kind of an acquired taste. I used to hate herbal teas because you couldn't put milk and sugar into them and that's like the _only   
_way that I could drink teas before but now I've become majorly obsessed with them. So obsessed that I drink like two or three a day to concentrate..I'm babbling again." she said blushing a little, making Barry laugh. "They have black tea. You can drink that right?"

"I actually don't like _tea _at all. Sorry."

"Oh." she said frowning a little. "Well, maybe you should get a soda or a juice?"

"Or I could get a chocolate milkshake." he said pointing to it on the menu. "Are they any good?"

Oliver scoffed loudly and Felicity kicked him hard under the table, making him moan a little.

"I haven't had one." she said turning her attention back to Barry. "But if you are having one, I might get one too. What the hell?"

"Then it's settled. Two chocolate milkshakes and a cappuccino. I'll go and order." he said standing up quickly. "I'll be right back guys."

Oliver watched as Barry joined the long line at the counter. _Good. He was going to be there for a while. _

"What's up with you, today?" Felicity snapped a little irritably.

"Excuse me?"

"You're acting like a.._jerk." _She said avoiding his eyes. "Can you _try _to be nicer to the guy? He looks up to you, Oliver. What has he done to you, anyway?"

_You mean other than hit on my girl and order a chocolate milkshake? _Oliver thought rolling his eyes. _She had to be kidding, right?!_

"I don't know. He's a_ kid._" Oliver said shrugging his shoulders a little.

"He's _my _age." she growled defensively. "Does that mean you see _me _as a kid, too?"

"No. Of course not. Look Felicity..."

"So, you just don't want to see me happy, then?" she asked crossing her hands over her chest.

"What? Of course I do. It's just. Felicity-"

"Then don't ruin this for me, Oliver. I actually really _like _this guy!" she said, cutting him off mid-sentence. "He's the first guy that I've liked..." _Since you. _"...In a long time." she said sighing heavily. "And I could be wrong...but I feel like he kinda likes me too. So I want to see where this goes."

"Felicity...I-"

"I'm being seriously, Oliver!" she snapped quickly.

"Felicity...I have been so_ blind _for so long and there's something that I need to tell you." Oliver started again, before she cut him off quickly.

"Okay, he's coming back. Please just try to cut him some slack, okay? _For me?"_ she asked pleadingly.

"Fine." he hissed, rolling his eyes a little and then faking a smile as Barry slid back into the booth next to Felicity.

-x-

"So where do you plan on staying while you're here?" Oliver asked Barry.

"I'm not too sure actually. Can you guys recommend any good cheap, but decent hotels?" he asked laughing casually. "I'd even settle for a student hostel or a fairly priced motel. Nothing too fancy, though."

"I have a spare room at my apartment." Felicity said blushing a little. Oliver snapped his head up and looked at her quickly."I mean, there's no bed...but there's a couch. You're welcome to crash there if you want."

"I'm sure he doesn't want to sleep on a couch, Felicity." Oliver said, trying his best to hide his apparent jealousy. "He will need a bed. I know a few cheap places-"

"I don't mind." Barry said quickly, cutting him off mid-sentence, before turning his attention to Felicity. "As long as I'm not invading your privacy or intruding in any way?"

"Of course not." she said smiling.

"I can pay you rent."

"Don't be silly." she said shaking her head quickly. "I'd be happy to have some company. You are welcome to stay as long as you like."

Oliver felt someone had just taken a sledge hammer to his heart and smashed it into a thousand tiny pieces.

"Felicity, can I have a quick word with you for a minute?" Oliver asked, as jealousy consumed him.

"Sure." she said frowning. "I'll be right back. Sorry."

They headed towards the back of the cafe and out towards its courtyard. All it was packed with people, it was a lot quieter than the inside of the busy cafe.

"What's up?' she asked, before pushing up her glasses.

"Look Felicity..." he started running a hand through his hair quickly. He had no idea how he was going to tell her what he needed to say. But he knew that he would feel so much better to get it off his chest.

"Oliver?" she asked frowning a little, when he had said nothing further.

"I don't think Barry should be staying with you." he blurted out quickly.

"What?"

"I think it's a bad idea."

"Really?" she snapped defensively. "And why is that?"

"Because how _well_ do you really know this guy? I mean you haven't known him for that long."

Felicity scoffed loudly. "I think I know him pretty well, Oliver. We have been chatting every day for the past two months. He seems nice enough."_  
_

"I just don't want to see you get hurt."

"You don't want to see me get hurt? Or you don't want to see me with him?" she asked, raising a perfectly arched eyebrow. "Oliver you are _acting _like a jealous boyfriend!"

"That's because I am _jealous, _okay?" he growled angrily, making her jump a little.

"What?" she mumbled quietly.

"I'm jealous, Felicity. I like you." he said, his tone a little softer this time. "I like you a lot and yes, I don't want to see you with him."

"_Why now_?" she asked as tears filled her eyes. "Why are you telling me this now? What changed your mind? Was it that somebody else finally showed some interest in me? Is that it?"

"No. Of course not." Oliver said placing both of his hands on her shoulders quickly.

Felicity brushed him off quickly and took a step back to distance herself from him.

"Felicity, I've been so _blind_." he said softly. "I've let some many things get in the way of my feelings for you. My work...the arrow stuff..my complicated family life."

"Laurel. Helena. McKenna. Sarah." she snapped angrily, naming all his previous girlfriends in order.

"Felicity...I was only trying to keep you safe. I never wanted to put a target on your back. I cared about you too much."

"That's right." she said sarcastically, as tears burned at her eyes. "I remember your whole speech Oliver. Word for word... '_because of the life I lead, I think it's best that I not be with someone I could really care about' _You know I almost believed you back then. But Starling City has been safe for months now. We defeated Slade and his army and nothing has happened for three months!"

"Felicity..."

"THREE MONTHS, OLIVER." she repeated loudly, shaking her head from side to side. "So excuse me, if I don't believe you. Your reasoning is pretty worthless now." she said, turning on her heel to storm off.

"Felicity, wait!" he said, grabbing her hand quickly and stopping her dead in her tracks. "I'm sorry that I waited so long to make a move. I wanted to make sure that I wouldn't be putting you into harm's way. The City might be safe now, but we are always under attack. _You, _of all people should know that. I'm always thinking of your best interests. I love you, Felicity. I have for a while and I'm sorry that my timing is off. I'm sorry that I didn't tell you how I felt earlier or that I made you ever question my feelings for you. But I am telling you now. I love you and I know you feel the same way about me. So all I'm asking is that you don't start anything with Barry and that you give us a go."_  
_

"I'm sorry, Oliver but I can't do that." she said softly, as she wiped away a few tears that streaked down her face. "I waited _forever _for you to say something like that to me. If only you knew _how long _I've waited...But I can't go out with somebody who _only_ wants me when he's scared that he's _loosing me_ to somebody else. That's not how love works."

"Felicity, please...just go on a date with me. One date tonight and then you can decide. Please, I know that you feel the same way as I do."

"I don't anymore." she snapped quickly. "I _used _to...but I got _over_ you, Oliver. I waited and waited...I had no idea that you even felt _anything _for me other than friendship, so I decided to move on. I couldn't wait forever. Barry helped me move on from you."

"Felicity..."

"I should go. We left Barry all alone." she said pushing past him.

He wanted to stop her. To grab her and kiss her. To do some grand romantic gesture to show her how much he cared for her and that his feelings were real. He wanted to test whether she still felt sometime for him. Anything.

But he decided to let her go. Even though it was killing him inside. He knew it was the right thing to do.

Oliver sighed heavily. She had been right there under his nose the whole time and he had left it too long. _He had lost her._

_She was over him. He had lost his chance to be with her now and maybe even forever, _he thought as he stood stunned in the packed courtyard. _How on earth had he ever been so stupid?!_

_The end._

** Author's note:**

Sorry if the ending was kind of a downer or not as happy as you would like it to be. A reviewer asked for a drabble where Felicity said NO and hence the ending for this installment. To be honest, I had a few more ideas for drabbles, but I think I'm going to call it quits.

I don't think anyone is really enjoying this since I'm hardly getting any reviews or feedback. I might just focus on my other stories that need updating or work on my other Olicity story.

To those of you who read and reviewed...thank you from the bottom of my heart. After the hours of writing (after work when I'm dead tired) and all the editing/proof reading that goes into an update..it's always so rewarding to have some appreciate your work. So thank you :) I hope you've enjoyed reading these as much as I have enjoyed writing them :)

Paris xx


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